1. Field of the Invention
This invention relates to novel N-sulfonyl phosphorodiamido(di)thioate compounds, to compositions thereof which are useful are pesticides, more specifically as acaricides, insecticides, and nematocides, and to a method of controlling pests in agricultural plants. These compounds also exhibit fungicidal activity.
2. Description of the Prior Art
Ollinger, U.S. Pat. No. 4,315,870 issued Feb. 16, 1982 discloses acaricidal, insecticidal and nematicidal phosphorodiamidothioates represented by the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are selected from unsubstituted and substituted alkyl, alkenyl, alkynyl, phenyl, and phenylalkyl groups and X and X.sup.1 are selected from oxygen and sulfur atoms.
Magee, U.S. Pat. No. 3,716,600, discloses insecticidal phosphoroamidothioates represented by the formula ##STR2## wherein R is C.sub.1 -C.sub.3 alkyl; R.sup.1 is C.sub.1 -C.sub.3 alkyl, alkenyl or alkynyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.3 alkyl; X is carbonyl or sulfonyl; and Y is oxygen or sulfur; when X is sulfonyl, R.sup.3 is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.8 cycloalkyl or phenyl; and when X is carbonyl, R.sup.3 is hydrogen, C.sub.1 -C.sub.18 containing 1-4 halogens selected from F and Cl and Br, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.18 alkynyl, a heterocyclic radical of 1 hetero oxygen, sulfur, or nitrogen atom and 4 or 5 annual C atoms and a total of 4 to 8 carbon atoms, C.sub.2 -C.sub.12 alkoxyalkyl, C.sub.2 -C.sub.12 alkylthioalkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 alkylthio, pheny, phenyl substituted with 1 or 2 C.sub.1 -C.sub.3 alkyl radicals or C.sub.1 -C.sub.3 alkoxy radicals or halogen atoms selected from F and Cl and Br or NO.sub.2 groups, styryl, phenyl (C.sub.1 -C.sub.3) alkyl, phenoxy (C.sub.1 -C.sub.3) alkyl, thiophenoxy (C.sub.1 -C.sub.3) alkyl, or phenoxy (C.sub.1 -C.sub.3) alkyl or thiophenoxy (C.sub.1 -C.sub.3) alkyl in which the aromatic moiety is substituted with halogens selected from F and Cl and Br or mono-nitro (C.sub.1 -C.sub.3) alkyl.
Kishino et al., U.S. Pat. Nos. 4,134,979 (Jan. 16, 1979) and 4,161,524 (July 17, 1979), disclose insecticidal, acaricidal and nematicidal O-alkyl-S-n-propyl-N-sulfonyl-phosphoric acid ester amides represented by the formula ##STR3## wherein R.sup.1 is methyl or ethyl; R.sup.2 is unsubstituted C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.1 -C.sub.6 alkyl substituted by aryl, phenyl, C.sub.1 -C.sub.6 alkylphenyl, or halophenyl; R.sup.3 is C.sub.1 -C.sub.6 alkylphenyl, C.sub.1 -C.sub.6 alkoxyphenyl, halophenyl, or nitrophenyl; and X is O or S.
Japanese Patent No. 5 2,128,325 (Derwent Abstract 87 421 Y/49) discloses insecticidal, nematocidal and miticidal organic phosphoric acid amide esters represented by the formula ##STR4## wherein R.sup.1 is methyl or ethyl; R.sup.2 is lower alkyl, alkenyl, aralkyl or phenyl substituted with up to three alkyl or halogen groups; R.sup.3 is lower alkyl, haloalkyl or phenylalkyl wherein the phenyl ring may be substituted with up to three substituents selected from lower alkyl, nitro or lower alkoxy; and X is O or S.